Mark T. Bertolini
Chief Executive Officer
Executive
3 yr
7 reports
Oscar Health, Inc. ·OSCR
Technology co-founder remains CTO under external CEO
Health Care · Fortune #437 · Hybrid structure · 2K employees · New York, New York
View as of:
5
CEO span
↓ tighter than peers (avg 8)
1.4
Avg span
tight
3
Max depth
3 levels
6 yr
Avg tenure
↑ 1.0yr from FY2024
60%
Internal hires
↑ above industry avg
Consolidated financials FY2025 · period end 2025-12-31 · 10-K
Revenue
$29M
Operating income
$-396357000
Net income
$-443151000
Total assets
$6.3B
Sourced from Oscar Health, Inc. DEF 14A · filed 2026-04-22 ↗ View on SEC
Interactive org chart
Oscar Health, Inc. organizational chart
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Technology co-founder Mario Schlosser continues as CTO under externally hired CEO Mark Bertolini. This page maps Oscar Health’s hybrid structure, executive team, and governance, highlighting its founder-led technology core, shallow hierarchy, and recent leadership changes.
What to model
Use the chart to test org decisions, not just view reporting lines
Start with the public baseline, then use the scenario views and source-backed changes to ask what happens when leadership, span, or team ownership shifts.
Latest signal Mark T. Bertolini changed role as Chief Executive Officer
Amended and restated employment agreement executed December 22, 2025.
Source · See change logScenario views in the chart
- Add Chief Operating Officer Introduce a COO to integrate insurance operations and technology execution as the company scales.
- CTO Succession Planning Prepare for eventual transition from founder-led technology to a professional CTO successor.
Atlas work this supports
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The people
Who's running this
6 executives identified as Named Executive Officers in the most recent SEC proxy. Bar length scales with tenure.
internal
Mario Schlosser
Co-Founder, President of Technology and Chief Technology Officer
Technology
14 yr
0 reports
internal
R. Scott Blackley
Chief Financial Officer
Finance
5 yr
1 reports
Janet Liang
President of Oscar Insurance
Insurance Operations
1 yr
0 reports
Adam McAnaney
Chief Legal Officer
Legal
1 yr
1 reports
internal
Joshua Kushner
Co-Founder and Vice Chair of the Board
Board Leadership
14 yr
0 reports
The skin in the game
Beneficial ownership
Insider stock holdings and the company's ownership requirements for executives and directors. Disclosed in the most recent DEF 14A.
Stock ownership requirements
5×Director cash retainer
Directors must hold stock equal to at least 5x annual cash retainer.
The businesses
How Oscar Health, Inc. divides the work
3 divisions report into the group CEO. Tile size scales with estimated headcount.
Technology
900 employees
President of Technology & CTO (Mario Schlosser)
Builds and operates Oscar’s full-stack insurance and engagement technology platform.
Insurance Operations
800 employees
President of Oscar Insurance (Janet Liang)
Oversees health plan operations, medical management, and regulatory execution.
Finance
300 employees
Chief Financial Officer (Scott Blackley)
Manages financial reporting, capital, actuarial, and investor relations functions.
The thesis
Why this org is unusual
Oscar Health’s most distinctive structural feature is that its technology co-founder remains deeply embedded as CTO under an externally hired CEO.
Mark Bertolini, recruited in 2023, sits above a leadership bench where founder Mario Schlosser continues to run technology with broad autonomy.
The CEO’s span includes technology, finance, insurance operations, legal, and a founder–vice chair role, producing a hybrid structure that blends founder-led product control with professionalized insurance and financial management. Insurance operations are consolidated under Janet Liang, reflecting a shift toward execution discipline and regulatory scale.
The organization is relatively shallow, with only a few publicly named executives below the C-suite, consistent with Oscar’s technology-centric operating model and centralized decision-making.
- Founder CTO retained under external CEO
- No standalone COO role
The comparison
How Oscar Health, Inc. stacks up
Compared with other publicly traded managed-care and health-tech peers, Oscar Health maintains a smaller, more founder-influenced executive team. Unlike traditional insurers such as UnitedHealth or Elevance, Oscar concentrates technology and product authority under a single long-tenured founder-CTO. Peers of similar …
C-suite size
Reporting depth
Oscar Health, Inc.
3 levels
Clover Health
4 levels
Alignment Healthcare
5 levels
6 levels
6 levels
Avg C-suite tenure
Has COO / Has CAIO
Oscar Health, Inc. — no COO — no CAIO
Clover Health — no COO — no CAIO
Alignment Healthcare ✓ COO — no CAIO
Current signals
What changed recently
The most significant recent change was the hiring of Janet Liang as President of Oscar Insurance in February 2025.
Leadership Timeline
Year-over-year executive structure based on SEC proxy and annual filings.
FY2025
DEF 14A filed 2026-04-22
- CEO
- Mark T. Bertolini
- CEO span
- 5
- C-suite
- 5
- Avg tenure
- 6 yr
Founder CTO retained alongside externally hired CEO.
Named executive officers (5)
- Mark T. Bertolini - Chief Executive Officer since 2023
- Mario Schlosser - President of Technology & CTO since 2012
- Scott Blackley - Chief Financial Officer since 2021
- Janet Liang - President of Oscar Insurance since 2025
- Adam McAnaney - Chief Legal Officer since 2025
FY2024
DEF 14A filed 2025-04-25
- CEO
- Mark T. Bertolini
- CEO span
- 5
- C-suite
- 5
- Avg tenure
- 5 yr
Insurance and legal leadership later turned over in 2025.
Named executive officers (5)
- Mark T. Bertolini - Chief Executive Officer since 2023
- Mario Schlosser - President of Technology & CTO since 2012
- Scott Blackley - Chief Financial Officer since 2021
- Alessandrea Quane - Chief Insurance Officer since 2021
- Ranmali Bopitiya - Chief Legal Officer since 2021
FY2023
DEF 14A filed 2024-04-25
- CEO
- Mark T. Bertolini
- CEO span
- 4
- C-suite
- 4
- Avg tenure
- 4 yr
CEO transition from founder-led model.
Named executive officers (4)
- Mark T. Bertolini - Chief Executive Officer since 2023
- Mario Schlosser - CTO since 2012
- Scott Blackley - Chief Transformation Officer since 2022
- Ranmali Bopitiya - Chief Legal Officer since 2021
Year-over-year changes
Insurance and legal leadership turned over while overall structure remained stable.
- CEO span: 5 → 5
- C-suite size: 5 → 5
- Avg tenure: 5 → 6 yr
- new Janet Liang - President of Oscar Insurance (DEF 14A, Apr 2026)
- new Adam McAnaney - Chief Legal Officer (DEF 14A, Apr 2026)
The board
Board of directors
8 directors. 5 of 8 independent (63%). Source: most recent DEF 14A.
Joshua Kushner
Inside
Co-Founder, Thrive Capital
Mark T. Bertolini
Inside
Chief Executive Officer, Oscar Health
William (Bill) J. Gassen III
Independent
Laura Lang
Independent
David Alexander Plouffe
Independent
Siddhartha Sankaran
Independent
Mario Schlosser
Inside
CTO, Oscar Health
Vanessa Ames Wittman
Independent
Frequently Asked Questions
Who is the CEO of Oscar Health?
Mark T. Bertolini has served as CEO since April 2023.
What type of organizational structure does Oscar Health use?
Oscar Health uses a hybrid structure blending founder-led technology with functional insurance and finance leadership.
How many direct reports does Oscar Health's CEO have?
The CEO has five direct executive reports.
How has Oscar Health's leadership changed recently?
Recent changes include the hiring of Janet Liang as President of Oscar Insurance and Adam McAnaney as Chief Legal Officer in 2025.
Who reports directly to Oscar Health's CEO?
Direct reports include the CTO, CFO, President of Oscar Insurance, Chief Legal Officer, and Vice Chair.
Sources
- Form 8-K, Dec 29 2025
- Company Proxy Statement, Apr 2026
- SEC EDGAR: Oscar Health, Inc. DEF 14A Proxy Statement
- SEC EDGAR: Oscar Health, Inc. 10-K Annual Report
Reference
Cite this page
If you reference this page in research, analysis, or news writing, use one of the formats below. Citation includes the SEC filing source where applicable.
APA 7th
Creately. (2026). Oscar Health, Inc. organizational structure. Creately. Retrieved , from https://creately.com/org-chart/fortune-500/oscar-health/MLA 9th
"Oscar Health, Inc. Organizational Structure." Creately, April 1, 2026, https://creately.com/org-chart/fortune-500/oscar-health/. Accessed .Chicago 17
Creately. "Oscar Health, Inc. Organizational Structure." Last modified April 1, 2026. https://creately.com/org-chart/fortune-500/oscar-health/.Original SEC source View on SEC ↗
Oscar Health, Inc.. DEF 14A. Filed 2026-04-22. U.S. Securities and Exchange Commission. https://www.sec.gov/Archives/edgar/data/1568651/000114036126016119/ny20059895x771_def14a.htmPermanent URL: https://creately.com/org-chart/fortune-500/oscar-health/ · last updated 2026-04-01